Methylamine → HCID 59239031, compound

HRID 2060993Notes

Reaction equation

HRID 2060993 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[N:25](C(OC(C)(C)C)=O)[C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][C:31]=3[C:3]=12.[CH3:40][NH2:41].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+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[F:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:4]1[C:5]([O:23][CH3:24])=[C:6]3[NH:7][C:8]4[CH:9]=[CH:10][C:11]([F:15])=[CH:12][C:13]=4[C:14]3=[C:2]([NH:41][CH3:40])[C:3]2=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 67211859HCID 67211859, compound

Product 1

HCID 59239031HCID 59239031, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The title compound was prepared in a manner analogous to Example 133. This compound was obtained by heating di-tert-butyl 12-bromo-2,10-difluoro-6-methoxyindolo[2,3-b]carbazole-5,7-dicarboxylate and MeNH2 in a bomb, in the presence of Pd(OAc)2, BINAP, and NaOtBu at 80° C. overnight. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.17 (s, 2H), 8.06 (dd, J=10.2, 2.6 Hz, 2H), 7.39 (dd, J=8.8, 4.4 Hz, 2H), 7.14 (td, J=9.2, 2.4 Hz, 2H), 4.77 (q, J=5.6 Hz, 1H), 4.00 (s, 3H), 3.01 (d, J=5.6 Hz, 3H).

Workup

  1. customThis compound was obtained
  2. customat 80° C.
  3. customovernight

Sources & evidence

ORD record
ord-5b2cde2ab15747019f202381dcc3764f
Source dataset
uspto-grants-2012_10
Patent number
US08278341B2

Reaction notes

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