Trifluoroacetic acid → HCID 59238943, compound

HRID 1949121Notes

Reaction equation

HRID 1949121 reaction equation
Br[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([F:15])[CH:12]=3)[N:7](C(OC(C)(C)C)=O)[C:6]=2[C:5]([O:23][CH3:24])=[C:4]2[NH:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][C:31]=3[C:3]=12.[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].C(O)(C(F)(F)F)=O>CC([O-])=O.CC([O-])=O.[Pd+2]>[F:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[C:5]([O:23][CH3:24])=[C:4]3[NH:25][C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][C:31]=4[C:3]3=[C:2]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[C:14]2=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 67211816HCID 67211816, compound

Product 1

HCID 59238943HCID 59238943, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The title compound was prepared by the reaction tert-butyl 12-bromo-2,10-difluoro-6-methoxyindolo[2,3-b]carbazole-5(7H)-carboxylate with pyrrolidine in the presence of Pd(OAc)2, BINAP, and NaOtBu at 80° C. for 2 h, followed deprotection with TFA. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.29 (s, 2H), 7.70 (dd, J=10.0, 2.4 Hz, 2H), 7.43 (dd, J=8.8, 4.8 Hz, 2H), 7.19 (td, J=9.2, 2.4 Hz, 2H), 4.05 (s, 3H), 3.43-3.55 (m, 4H), 2.40-2.30 (m, 4H).

Sources & evidence

ORD record
ord-a690f15247e54b7dab7e21502639e725
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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