1-Bromo-2,3-dichlorobenzene → HCID 60088371, compound

HRID 1836578Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[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[C:7]([Cl:8])=[CH:6][CH:5]=[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

Reactant 2

HCID 420661-Bromo-2,3-dichlorobenzene

HCID 131724537HCID 131724537, compound

Product 1

HCID 60088371HCID 60088371, compound

Procedure

Using 2,3-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 74 as an off-white powder. 1H NMR (300 MHz, CDCl3) δ 1.25 (br s, 1H), 1.95-2.05 (m, 2H), 2.10-2.30 (m, 1H), 2.80 (m, 4H), 2.95 (t, 1H, J=9.5 Hz), 3.30-3.55 (m, 5H), 3.54 (dd, 1H, J=9.5, 7.0 Hz), 5.93 (br s, 1H), 6.50 (s, 1H), 6.71 (s, 2H), 6.74-6.79 (m, 1H), 6.92 (t, 1H, J=8.1 Hz). LRMS (ES)+: 374 (M+H)+.

Sources & evidence

ORD record: ord-a4bcef792abe419393292cb0f6c8f63f
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777406B2

Reaction notes

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