1-Bromo-2-(cyclopropylsulfonyl)benzene → 5-[2'-(Cyclopropylsulfonyl)-3-fluorobiphenyl-4-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 1523906Notes

Reaction equation

HRID 1523906 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[CH:18]=[C:19]2[CH:25]=[CH:24][NH:23][C:20]2=[N:21][CH:22]=1.Br[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([CH:36]1[CH2:38][CH2:37]1)(=[O:35])=[O:34]>>[CH:36]1([S:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:6]2[CH:5]=[CH:4][C:3]([C:17]3[CH:18]=[C:19]4[CH:25]=[CH:24][NH:23][C:20]4=[N:21][CH:22]=3)=[C:2]([F:1])[CH:7]=2)(=[O:34])=[O:35])[CH2:38][CH2:37]1

Participants

3

Reactant 2

HCID 681817441-Bromo-2-(cyclopropylsulfonyl)benzeneHCID 903129005-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 903136085-[2'-(Cyclopropylsulfonyl)-3-fluorobiphenyl-4-yl]-1H-pyrrolo[2,3-b]pyridine

Procedure

The title compound was prepared using methods analogous to those described in Example 376 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine and 1-bromo-2-(cyclopropylsulfonyl)benzene. MS (ESI): mass calcd. for C22H17FN2O2S, 392.10; m/z found, 393.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 9.26 (s, 1H), 8.62-8.52 (m, 1H), 8.24-8.12 (m, 2H), 7.71-7.63 (m, 1H), 7.62-7.53 (m, 2H), 7.45-7.31 (m, 4H), 6.64-6.55 (m, 1H), 2.19-2.08 (m, 1H), 1.18-1.08 (m, 2H), 0.93-0.82 (m, 2H).

Sources & evidence

ORD record
ord-2fe7431c92274181ba8e6fc7378f6046
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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