4-Bromo-1,2-dichlorobenzene → HCID 60088408, compound

HRID 1836577Notes

Reaction equation

HRID 1836577 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[Cl:8].[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:3]=[C:4]([NH:10][C:11]2[CH:12]=[C:13]3[C:18]4=[C:19]([CH2:21][CH2:22][CH2:23][N:17]4[CH2:16][C@@H:15]4[CH2:24][NH:25][CH2:26][C@@H:14]34)[CH:20]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 290134-Bromo-1,2-dichlorobenzeneHCID 131724537HCID 131724537, compound

Product 1

HCID 60088408HCID 60088408, compound

Procedure

Using 3,4-dichlorobromobenzene and following the procedures described in EXAMPLE 72, (±)-trans 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 was converted into the title compound of EXAMPLE 73 as a tan solid. 1H NMR (300 MHz, CDCl3) δ 1.25 (br s, 1H), 1.95 (m, 2H), 2.00 (m, 1H), 2.70 (m, 4H), 2.90 (t, 1H, J=9.7 Hz), 3.10-3.50 (m, 5H), 3.54 (t, 1H, J=9.7 Hz), 5.34 (br s, 1H), 6.42 (s, 1H), 6.51 (m, 1H), 6.59 (s, 1H), 6.83 (d, 1H, J=2.6 Hz), 7.16 (d, 1H, J=8.7 Hz). LRMS (ES)+: 374 (M+H)+.

Sources & evidence

ORD record
ord-ec639c1949534d48b8443bb25d9e298b
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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