Ethanol → HCID 11700489, compound

HRID 1158524Notes

Reaction equation

HRID 1158524 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][C:41](Br)=[CH:40][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].[S:46]1[C:50](B(O)O)=[CH:49][C:48]2[CH:54]=[CH:55][CH:56]=[CH:57][C:47]1=2.C([O-])([O-])=O.[Na+].[Na+].CCO>COCCOC>[CH3:1][O:2][C:3](=[O:45])[NH:4][C@H:5]([C:10]([NH:12][N:13]([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)[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([C:50]2[S:46][C:47]3[CH:57]=[CH:56][CH:55]=[CH:54][C:48]=3[CH:49]=2)=[CH:40][CH:39]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 702EthanolHCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 11513133HCID 11513133, compound

Product 1

HCID 11700489HCID 11700489, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound was prepared according to Method B, using 19 (83.4 mg, 0.123 mmol), benzo[b]thiophene-2-boronic acid (109 mg, 0.613 mmol), Pd(PPh)3Cl2 (4.32 mg, 0.00615 mmol), 2 M Na2CO3 (aq., 0.185 mL, 0.369 mmol), EtOH (0.4 mL) and DME (1.6 mL). Purification by RP-LC-MS (35 min gradient of 20-100% CH3CN in 0.05% aqueous formic acid) afforded the product (56.4 mg, 62%) as a white solid.

Workup

  1. customPurification by RP-LC-MS (35 min gradient of 20-100% CH3CN in 0.05% aqueous formic acid)

Sources & evidence

ORD record
ord-070e1b840a684dc4bad2f0fed6a4ee60
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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