1154741-01-1 → HCID 71209390, compound

HRID 1912625Notes

Reaction equation

HRID 1912625 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:12](I)=[C:13]2[CH:20]=[CH:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:31][C:32]1([CH3:50])[C:36]2[CH:37]=[C:38](B3OC(C)(C)C(C)(C)O3)[CH:39]=[CH:40][C:35]=2[O:34][CH2:33]1>>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([C:38]2[CH:39]=[CH:40][C:35]3[O:34][CH2:33][C:32]([CH3:31])([CH3:50])[C:36]=3[CH:37]=2)=[C:13]2[CH:20]=[CH:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 596067741154741-01-1HCID 71209175HCID 71209175, compound

Product 1

HCID 71209390HCID 71209390, compoundYield 84%

Procedure

The title compound was prepared in a manner similar to that described in Example 87 from (S)-methyl 2-(tert-butoxy)-2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate and 2-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (WO2009/062285) to afford the title compound (76 mg, 84%) after purification by reverse phase HPLC. 1H NMR (400 MHz, DMSO-d6, VT) δ ppm 7.49-7.19 (m, 5 H), 7.16 (d, J=2.0 Hz, 1 H), 6.92 (d, J=8.2 Hz, 1 H), 6.10 (br. s., 1 H), 5.42 (d, J=2.7 Hz, 2 H), 5.31 (s, 1 H), 4.32 (s, 2 H), 2.66-2.59 (s, 3 H), 1.42-1.32 (br. s., 3 H), 1.27 (br. s., 3H), 0.84 (s, 9 H); LC/MS ES+=535.52 (M+1).

Workup

  1. customThe title compound was prepared in a manner similar to

Sources & evidence

ORD record
ord-3a7aaacc693e46cdbfa79f22c4b15379
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

Loading…