Trimethyl borate → HCID 145857613, compound

HRID 723054Notes

Reaction equation

HRID 723054 reaction equation
C([Li])CCC.COB(OC)OC.Br[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH:21]([O:24][CH3:25])[O:22][CH3:23])[CH:15]=1.[C:26]([O:30][C:31](=[O:52])[NH:32][C:33]([C:35]1[S:36][C:37]([S:50][CH3:51])=[C:38]([S:40]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45](Br)[CH:44]=2)(=[O:42])=[O:41])[CH:39]=1)=[NH:34])([CH3:29])([CH3:28])[CH3:27].C([O-])([O-])=O.[Na+].[Na+].[CH3:59][O:60][CH:61]([O:72][CH3:73])[C:62]1[CH:67]=[C:66]([OH:68])[CH:65]=[CH:64][C:63]=1[B:69]([OH:71])[OH:70]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(O)C>[CH3:73][O:72][CH:61]([O:60][CH3:59])[C:62]1[CH:67]=[C:66]([OH:68])[CH:65]=[CH:64][C:63]=1[B:69]([OH:71])[OH:70].[C:26]([O:30][C:31](=[O:52])[NH:32][C:33]([C:35]1[S:36][C:37]([S:50][CH3:51])=[C:38]([S:40]([C:43]2[CH:44]=[C:45]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH:21]([O:24][CH3:25])[O:22][CH3:23])[CH:15]=3)[CH:46]=[CH:47][CH:48]=2)(=[O:42])=[O:41])[CH:39]=1)=[NH:34])([CH3:29])([CH3:28])[CH3:27]

Participants

11

Reactant 6

HCID 8470Trimethyl borateHCID 10340Sodium CarbonateHCID 21886104HCID 21886104, compoundHCID 21886331HCID 21886331, compoundHCID 145857672tert-butyl N-[4-(3-bromophenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateHCID 178418339Butyllithium

Product 2

HCID 21886331HCID 21886331, compoundHCID 145857613HCID 145857613, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

2-Dimethoxymethyl-4-hydroxyl phenylboronic acid (212 mg, 1.0 mmol) was prepared using the procedure described in Example 1: step b using butyllithium (2.5M, 2.8 mL, 7 mmol), trimethylborate (0.812 mL, 5.6 mmol), 4-bromo-2-dimethoxymethyl-phenol (685 mg, 2.8 mmol, Example 26: step a) in THF (5 mL) and was used in the next step without purification. The procedure described in Example 1: step c was followed using {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (100 mg, 0.21 mmol, Example 27: step c), Pd(PPh3)4 (47 mg, 0.04 mmol), aqueous Na2CO3 (2M, 0.8 mL, 1.6 mmol), ethanol (0.8 mL), toluene (1.6 mL) and 2-dimethoxymethyl-4-hydroxy-phenylboronic acid (212 mg, 1.0 mmol). Purification by preparative SiO2 TLC (33% EtOAc in hexanes) of the residue yielded the title compound (37 mg, 28%) as a white solid. ESI-MS (m/z): Calcd. for C26H30N2O7S3: 579.1 (M+1); found: 579.9.

Workup

  1. customstep a) in THF (5 mL) and was used in the next step without purification
  2. customPurification by preparative SiO2 TLC (33% EtOAc in hexanes) of the residue

Sources & evidence

ORD record
ord-69c6bff87a1d498d86308fdaf4044249
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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