(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine → HCID 25114919, compound

HRID 1099408Notes

Reaction equation

HRID 1099408 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:46][CH3:47])=[C:40]([CH:45]=1)[C:41]([NH:43][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:46][CH3:47])=[C:40]([CH:45]=2)[C:41]([NH:43][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 251149185-bromo-2-methoxy-N-methylnicotinamide

Product 1

HCID 25114919HCID 25114919, compoundYield 66%

Procedure

The title compound was synthesized as described for Intermediate I-28 in 66% 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-methylnicotinamide; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.33 (q, 1 H), 8.29 (d, 1 H), 8.06 (d, 1 H), 7.24-7.32 (m, 8 H), 7.11-7.21 (m, 3 H), 6.71-6.82 (m, 2 H), 4.26-4.38 (m, 1 H), 4.04 (s, 3 H), 4.01-4.11 (m, 1 H), 3.57-3.73 (m, 4 H), 2.87-3.09 (m, 2 H), 2.84 (d, 3 H), 2.46-2.54 (m, 1 H, obscured by DMSO); MS (ESI) m/z 494[M+H+].

Sources & evidence

ORD record
ord-469dad0befcb444d8cef0f0a0d65974b
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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