N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine hydrochloride → HCID 67814748, compound

HRID 1616803Notes

Reaction equation

HRID 1616803 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH:13][CH2:14][C:15]3[C:16](=[O:25])[NH:17][C:18]([CH3:24])=[CH:19][C:20]=3[CH2:21][CH2:22][CH3:23])=[O:12])[CH:10]=1)[N:7]([CH3:26])[CH:6]=[C:5]2[CH:27]([CH3:29])[CH3:28].Cl.[CH3:31][N:32]([CH2:34][C:35]1[CH:36]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:38]=[CH:39][CH:40]=1)[CH3:33]>>[CH3:31][N:32]([CH2:34][C:35]1[CH:40]=[C:39]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([C:11]([NH:13][CH2:14][C:15]4[C:16](=[O:25])[NH:17][C:18]([CH3:24])=[CH:19][C:20]=4[CH2:21][CH2:22][CH3:23])=[O:12])[CH:10]=2)[N:7]([CH3:26])[CH:6]=[C:5]3[CH:27]([CH3:28])[CH3:29])[CH:38]=[CH:37][CH:36]=1)[CH3:33]

Participants

3

Reactant 2

HCID 44118822N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine hydrochlorideHCID 67816516HCID 67816516, compound

Product 1

HCID 67814748HCID 67814748, compoundYield 63%

Procedure

The title compound was prepared in the same manner as described for Example 2 using 5-bromo-1-methyl-3-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indole-7-carboxamide (300 mg, 0.65 mmol) and 3-(N,N-dimethylaminomethyl)phenylboronic acid pinacol ester hydrochloride (250 mg, 0.84 mmol). Obtained 210 mg of the title compound (63% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.50 (s, 1H), 8.49 (t, J=4.80 Hz, 1H), 7.82 (d, J=1.77 Hz, 1H), 7.56-7.64 (m, 2H), 7.41 (t, J=7.58 Hz, 1H), 7.31 (d, J=1.52 Hz, 1H), 7.25 (d, J=7.58 Hz, 1H), 7.11 (s, 1H), 5.91 (s, 1H), 4.38 (d, J=5.05 Hz, 2H), 3.70 (s, 3H), 3.33 (s, 2H), 3.22 (quin, J=6.76 Hz, 1H), 2.52-2.59 (m, J=6.82, 8.59 Hz, 2H), 2.26 (br. s., 6H), 2.13 (s, 3H), 1.58 (sxt, J=7.53 Hz, 2H), 1.31 (d, J=6.82 Hz, 6H), 0.94 (t, J=7.33 Hz, 3H). MS (ES) [M+H]+ 513.3.

Workup

  1. customThe title compound was prepared in the same manner

Sources & evidence

ORD record
ord-b48bba47c5d74c44bce8dd02b78d2a3a
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

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