4-(Methylcarbamoyl)benzeneboronic acid → 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-N-methylbenzamide

HRID 1676281Notes

Reaction equation

HRID 1676281 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17](I)[S:18][C:11]=12)[NH2:5].[CH3:20][NH:21][C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23]>>[NH2:5][C:4]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[CH:16]=[C:17]([C:27]4[CH:28]=[CH:29][C:24]([C:22]([NH:21][CH3:20])=[O:23])=[CH:25][CH:26]=4)[S:18][C:11]=23)=[C:2]([F:1])[CH:3]=1

Participants

3

Reactant 2

HCID 27735264-(Methylcarbamoyl)benzeneboronic acidHCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

Product 1

HCID 673486984-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-N-methylbenzamideYield 96%

Procedure

Prepared from 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 0.300 g, 0.777 mmol) and 4-(methylcarbamoyl)phenylboronic acid (0.174 g, 0.971 mmol) according to the procedure described for Example 94, Step A. Purified by trituration from hot MeOH to obtain the product (210 mg, 96%) as a brown solid. LRMS (APCI pos) m/e 394 (M+1).

Workup

  1. customPurified by trituration from hot MeOH

Sources & evidence

ORD record
ord-cc6500c8e9f3449fac96d5333fb78dc6
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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