Potassium Bromide → HCID 67379676, compound

HRID 1951342Notes

Reaction equation

[N:1]([C:4](=[CH:10][C:11]1[C:12]2[N:13]([CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[N:19]=2)[CH:14]=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-].[K+].[Br-]>>[CH3:27][O:26][C:22]1[CH:21]=[C:20]([C:18]2[CH2:17][N:13]3[CH:14]=[CH:15][C:16]4[C:11]([CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:1]=4)=[C:12]3[N:19]=2)[CH:25]=[CH:24][CH:23]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 75147862HCID 75147862, compound

Product 1

HCID 67379676HCID 67379676, compound

Procedure

From 6d (yield: 50%); mp 198-200° C.; IR (KBr) 3297, 1670, 1261 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 1.41 (t, 3H, J=7 Hz), 3.90 (s, 3H), 4.41 (q, 2H, J=7 Hz), 6.88 (m, 2H), 7.34 (t, 1H, J=8 Hz), 7.52 (d, 2H, J=8 Hz), 7.58 (s, 1H), 7.74 (s, 1H), 7.76 (s, 1H), 7.88 (d, 1H, J=7 Hz), 9.93 (brs, 1H); 13C NMR (100 MHz, DMSO-d6) δ 14.3, 54.9, 60.5, 101.8, 106.8, 110.0, 110.4, 112.9, 113.2, 117.6, 124.3, 125.9, 129.7, 133.2, 135.6, 141.0, 141.9, 159.6, 160.6; MS m/z 335 (M+, 69), 289 (100), 132 (15), 102 (17). Anal. Calcd for C19H17N3O3: C, 68.05; H, 5.11; N, 12.53. Found: C, 68.23; H, 5.04; N, 12.73.

Sources & evidence

ORD record: ord-fb3105d093e745fc80ade6f5c97cdc90
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404707B2

Reaction notes

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