(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine → 5-[(3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl]-2-methoxy-N,N-dimethylnicotinamide

HRID 1099406Notes

Reaction equation

HRID 1099406 reaction equation
[CH2:1]([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2B2OC(C)(C)C(C)(C)O2)[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:36]1[CH:37]=[N:38][C:39]([O:47][CH3:48])=[C:40]([CH:46]=1)[C:41]([N:43]([CH3:45])[CH3:44])=[O:42]>>[CH2:28]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[C:36]2[CH:37]=[N:38][C:39]([O:47][CH3:48])=[C:40]([CH:46]=2)[C:41]([N:43]([CH3:45])[CH3:44])=[O:42])[O:11][CH2:10]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 25114260(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amineHCID 251149155-bromo-2-methoxy-N,N-dimethylnicotinamide

Product 1

HCID 251149165-[(3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl]-2-methoxy-N,N-dimethylnicotinamideYield 38%

Procedure

The title compound was synthesized as described for Intermediate I-28 in 38% yield starting from (3S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman -3-amine and 5-bromo-2-methoxy-N,N-dimethylnicotinamide. The reaction mixture was irradiated in a microwave at 140° C. for 45 min: 1H NMR (400 MHz, DMSO-d6) ppm 8.19 (d, 1 H), 7.68 (d, 1 H), 7.25-7.40 (m, 8 H), 7.11-7.22 (m, 3 H), 6.70-6.80 (m, 2 H), 4.32-4.38 (m, 1 H), 3.97-4.04 (m, 1 H), 3.96 (s, 3 H), 3.62-3.75 (m, 4 H), 3.02-3.13 (m, 2 H), 2.99 (s, 3 H), 2.91-2.98 (m, 1 H), 2.85 (s, 3 H); MS (ESI) m/z 508[M+H+].

Workup

  1. customThe reaction mixture was irradiated in a microwave at 140° C. for 45 min

Sources & evidence

ORD record
ord-0e71856a01184d7f918f97b7cef67de9
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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