2,6-Dichlorobenzeneboronic acid → HCID 9997654, compound

HRID 1292903Notes

Reaction equation

HRID 1292903 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([CH2:11][CH2:12][N:7]3[C@H:6]3[CH2:13][CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16][C@@H:5]23)[CH:10]=1.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=1B(O)O>>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=1[C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([CH2:11][CH2:12][N:7]3[C@H:6]3[CH2:13][CH2:14][NH:15][CH2:16][C@@H:5]23)[CH:10]=1

Participants

3

Reactant 2

HCID 27343322,6-Dichlorobenzeneboronic acidHCID 20577007Tert-butyl (6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate

Product 1

HCID 9997654HCID 9997654, compound

Procedure

The title compound was prepared by Example 305, Step A, from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate and the corresponding 2,6-dichlorobenzeneboronic acid followed by hydrolysis of the resultant BOC protected amine adduct by the procedure of Example 305, Step B. 1H NMR (CDCl3, 300 MHz) δ 7.38 (dd, 2H), 7.15 (t, 1H), 6.80 (d, 1H), 6.73 (d, 1H), 3.69 (td, 1H), 3.57-3.30(m, 3H), 3.28-3.00 (m, 3H), 3.00-2.83 (m, 3H), 2.20 (bs, 2H), 2.00-1.81 (m, 2H). MS (CI): 346 (M+H+).

Sources & evidence

ORD record
ord-9c1dbb0a6f14439b9aba35d6ea6218bb
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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