1H-Indole-4-boronic acid, pinacol ester → HCID 59151293, compound

HRID 2365192Notes

Reaction equation

HRID 2365192 reaction equation
[CH2:1]([N:8]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[S:28][C:27]3[C:26]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[N:25][C:24](Cl)=[N:23][C:22]=3[CH:21]=2)[CH2:15][CH2:14]1)[CH2:9][CH2:10][O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:44]2[CH:52]=[CH:51][CH:50]=[C:49]3[C:45]=2[CH:46]=[CH:47][NH:48]3)O1>>[CH2:1]([N:8]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[S:28][C:27]3[C:26]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[N:25][C:24]([C:44]4[CH:52]=[CH:51][CH:50]=[C:49]5[C:45]=4[CH:46]=[CH:47][NH:48]5)=[N:23][C:22]=3[CH:21]=2)[CH2:15][CH2:14]1)[CH2:9][CH2:10][O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 86638093HCID 86638093, compound

Product 1

HCID 59151293HCID 59151293, compound

Procedure

Benzyl-[1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-ylmethyl)-piperidin-4-yl]-(2-methoxy-ethyl)-amine (150 mg), was used in a Suzuki coupling with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (141 mg), to give after flash silica purification the title compound (105 mg) as a white solid.

Workup

  1. customto give
  2. customafter flash silica purification the title compound (105 mg) as a white solid

Sources & evidence

ORD record
ord-d029799306554fac94136711e98c857a
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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