Hydrochloric Acid → HCID 68467336, compound

HRID 2233065Notes

Reaction equation

HRID 2233065 reaction equation
[CH3:1][O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3=[CH:17][C:18]4[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:26])([CH3:25])[C:23]=4[CH:24]=[C:15]3[N:14]([CH3:29])[C:13]3[CH:30]=[CH:31][C:32]([B:34]4[O:38]C(C)(C)C(C)(C)[O:35]4)=[CH:33][C:12]=3[N:11]=2)=[CH:6][CH:5]=1.C1(B(O)O)C=CC=CC=1.Cl>>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:16]3=[CH:17][C:18]4[C:19]([CH3:28])([CH3:27])[CH2:20][CH2:21][C:22]([CH3:25])([CH3:26])[C:23]=4[CH:24]=[C:15]3[N:14]([CH3:29])[C:13]3[CH:30]=[CH:31][C:32]([B:34]([OH:35])[OH:38])=[CH:33][C:12]=3[N:11]=2)=[CH:8][CH:9]=1)=[O:43]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 66827Phenylboronic AcidHCID 68466574HCID 68466574, compound

Product 1

HCID 68467336HCID 68467336, compound

Procedure

A solution of 4-[5,7,7,10,10-pentamethyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-7,8,9,10-tetrahydro-5H-5,13diazabenzo[4,5]cyclohepta[1,2-b]naphthalen-12-yl]benzoic acid methyl ester (17) (R5=CH3, Z=H, 0.89 mmol) and phenyl boronic acid (1.8 mmol) in THF(=tetrahydrofuran)/MeOH (4:3, 14 mL) is treated with 2 N HCl (14 mL). After stirring for 5 h, the mixture is extracted with EtOAc. The extract is washed with brine, dried over MgSO4 and evaporated in vacuo. The resulting residue is purified by flash column chromatography (SiO2; hexane: EtOAc 4:1 to 1:1) to give 12-(4-methoxycarbonylphenyl)-5,7,7,10,10-pentamethyl-7,8,9,10-tetrahydro-5H-5,13-diazabenzo[4,5]cyclohepta[1,2-b]naphthalene-2-boronic acid (18) (R4=CH3, Z=H) contaminated with phenyl boronic acid.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washThe extract is washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe resulting residue is purified by flash column chromatography (SiO2; hexane: EtOAc 4:1 to 1:1)

Sources & evidence

ORD record
ord-f2092b4b09b740b0bf810c5c689fa443
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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