2-Bromo-1,4-dichlorobenzene → HCID 68525367, compound

HRID 1836570Notes

Reaction equation

HRID 1836570 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1Br.[NH2:10][C:11]1[CH:12]=[C:13]2[C:18]3=[C:19]([CH2:21][CH2:22][CH2:23][N:17]3[CH2:16][C@@H:15]3[CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][C@H:14]23)[CH:20]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:10][C:11]1[CH:12]=[C:13]2[C:18]3=[C:19]([CH2:21][CH2:22][CH2:23][N:17]3[CH2:16][C@@H:15]3[CH2:24][NH:25][CH2:26][C@H:14]23)[CH:20]=1

Participants

3

Reactant 2

HCID 150332-Bromo-1,4-dichlorobenzeneHCID 23518418HCID 23518418, compound

Product 1

HCID 68525367HCID 68525367, compound

Procedure

Using 2,5-dichloro-1-bromobenzene and following the procedures described in EXAMPLE 17, Parts B and C, (±)-cis-tert-butyl 2-amino-5,6,8a,9,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline-10(8H)-carboxylate, from EXAMPLE 17, Part A, was converted to the title compound of EXAMPLE 19. 1H NMR (CDCl3): δ 7.18 (d, 1H, J=8.4 Hz), 6.86 (d, 1H, J=2.2 Hz), 6.74 (s, 1H), 6.70 (s, 1H), 6.62 (dd, 1H, J=8.4, 2.6 Hz), 5.87 (s, 1H), 3.48-3.30 (m, 2H), 3.21 (q, 1H, J=7.6 Hz), 3.13-3.05 (m, 2H), 2.99 (dd, 1H, J=11.0, 4.7 Hz), 2.92-2.83 (m, 1H), 2.81-2.70 (m, 4H), 2.69-2.58 (m, 1H), 2.08-1.98 (m, 2H). LRMS (ES)+: 374.3 (M+H)+.

Sources & evidence

ORD record
ord-ad727ce6774d441bbaec3f0500825f6f
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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