3-Bromo-5-methoxypyridine → 4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-[5-(methyloxy)pyridin-3-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 241116Notes

Reaction equation

HRID 241116 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[CH3:10][C:11]1([CH3:35])[CH2:20][CH2:19][C:18]2[N:17]=[CH:16][N:15]=[C:14]([N:21]3[CH2:27][C:26]4[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][C:25]=4[O:24][CH2:23][CH2:22]3)[C:13]=2[CH2:12]1>>[CH3:10][C:11]1([CH3:35])[CH2:20][CH2:19][C:18]2[N:17]=[CH:16][N:15]=[C:14]([N:21]3[CH2:27][C:26]4[CH:28]=[C:29]([C:2]5[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=5)[CH:30]=[CH:31][C:25]=4[O:24][CH2:23][CH2:22]3)[C:13]=2[CH2:12]1

Participants

3

Reactant 2

HCID 8171633-Bromo-5-methoxypyridineHCID 66820411[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid

Product 1

HCID 498066364-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-[5-(methyloxy)pyridin-3-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepine

Procedure

Prepared according to the method of example 5 by using 3-bromo-5-methoxypyridine and [4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]boronic acid (reagent preparation 23) in step 1. 1H NMR (400 MHz, DMSO-d6): 8.49 (s, 1H), 8.40 (s, 1H), 8.26 (s, 1H), 7.75 (s, 1H), 7.59 (m, 2H), 7.07 (d, 1H), 4.65 (s, 2H), 4.35 (m, 2H), 3.90 (s, 3H), 3.84 (m, 2H), 2.67 (t, 2H), 2.44 (s, 2H), 1.57 (t, 2H), 0.82 (s, 6H); MS (EI) for C25H28N4O2: 417 (MH+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ff7687137f784603a860fc9de0a2d334
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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