1,2-Dimethoxyethane → HCID 11571120, compound

HRID 1158529Notes

Reaction equation

HRID 1158529 reaction equation
[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:10]([NH:12][N:13]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40](Br)[CH:39]=1)[CH2:14][C@:15]([OH:36])([C:23](=[O:35])[NH:24][C@H:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C@H:26]1[OH:34])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7].[C:46]1(B(O)O)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>C(O)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC#N.CCO>[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:10]([NH:12][N:13]([CH2:37][C:38]1[CH:39]=[C:40]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:41]=[CH:42][CH:43]=1)[CH2:14][C@:15]([OH:36])([C:23](=[O:35])[NH:24][C@H:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C@H:26]1[OH:34])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

9

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 11693236HCID 11693236, compound

Product 1

HCID 11571120HCID 11571120, compound

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 284Formic AcidSolventHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared according to Method B using compound 26 (80.5 mg, 0.118 mmol), phenylboronic acid (72.5 mg, 0.595 mmol), Pd(PPh3)2Cl2 (6.50 mg, 0.00926 mmol), 2 M Na2CO3 (aq., 0.177 mL, 0.354 mmol), DME (1.6 mL) and EtOH (0.4 mL) affording the product (21.2 mg, 26%) after RP-LC-MS (35 min gradient of 40-100% CH3CN in 0.05% aqueous formic acid) as a white solid.

Sources & evidence

ORD record
ord-71189a536ac74e03ba4662f013a3164c
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

Loading…