1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indole → HCID 59620093, compound

HRID 445597Notes

Reaction equation

HRID 445597 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:32]=2)[CH2:27][CH2:26]1>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:30]5[CH:29]=[C:28]6[C:33](=[CH:32][CH:31]=5)[N:25]([CH3:24])[CH2:26][CH2:27]6)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:23])[C:13]2=[O:22])[C:16]([CH3:21])=[N:17]1

Participants

3

Reactant 2

HCID 242295911-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indoleHCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Product 1

HCID 59620093HCID 59620093, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A, 40 mg, 0.106 mmol) and 1-methylindoline-5-boronic acid pinacol ester (Maybridge, Basel, Switzerland, 34 mg, 0.127 mmol) to give the title compound as a yellow solid. (HPLC: tR 2.52 min (Method A); M+H=425 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.87 (s, 1H), 8.16 (s, 1H), 8.00-7.97 (m, 1H), 7.83-7.81 (m, 1H), 7.41-7.40 (m, 1H), 7.20-7.17 (m, 1H), 7.14-7.13 (m, 1H), 6.57-6.55 (m, 1H), 3.94 (s, 3H), 3.56 (s, 3H), 3.33-3.29 (m, 2H), 2.92 (t, 2H), 2.73 (s, 3H), 1.94 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-0fc1c4bc9ad3406d8ae47ddaa6fd19b3
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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