4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide → 3'-(8-Methyl-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-4-sulfonic acid amide

HRID 1787424Notes

Reaction equation

HRID 1787424 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH2:14][C:13](=[O:15])[NH:12][C:11]3[CH:16]=[C:17]([C:21]([F:24])([F:23])[F:22])[C:18]([CH3:20])=[CH:19][C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:33]2[CH:38]=[CH:37][C:36]([S:39]([NH2:42])(=[O:41])=[O:40])=[CH:35][CH:34]=2)O1>>[CH3:20][C:18]1[C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:11]2[NH:12][C:13](=[O:15])[CH2:14][C:8]([C:4]3[CH:3]=[C:2]([C:33]4[CH:38]=[CH:37][C:36]([S:39]([NH2:42])(=[O:41])=[O:40])=[CH:35][CH:34]=4)[CH:7]=[CH:6][CH:5]=3)=[N:9][C:10]=2[CH:19]=1

Participants

3

Reactant 2

HCID 164141904-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamideHCID 673614604-(3-Bromo-phenyl)-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 250521603'-(8-Methyl-4-oxo-7-trifluoromethyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-biphenyl-4-sulfonic acid amide

Procedure

The title compound was prepared from 4-(3-bromo-phenyl)-7-methyl-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example B.1) (200 mg, 0.50 mmol) and commercially available 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenesulfonamide [CAS-no. 214360-51-7] (170 mg, 0.60 mmol) according to the general procedure II. Obtained as a white solid (165 mg, 69%). MS (ISP) 473.9 [(M+H)+]; mp>260° C.

Sources & evidence

ORD record
ord-f7e54c41871d45068095c800ea1d96b8
Source dataset
uspto-grants-2009_03
Patent number
US07511033B2

Reaction notes

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