Trifluoroacetic acid → HCID 58362567, compound

HRID 2361524Notes

Reaction equation

HRID 2361524 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=[C:4]2[N:3]=1.[NH:15]1[C:23]2[C:18](=[CH:19][C:20](B(O)O)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1.C(O)(C(F)(F)F)=O>O.CC#N>[NH:15]1[C:23]2[C:18](=[CH:19][C:20]([C:2]3[CH:7]=[CH:6][N:5]4[C:8]5[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=5[N:10]=[C:4]4[N:3]=3)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 27343615-Indolylboronic acidHCID 58362356HCID 58362356, compound

Product 1

HCID 58362567HCID 58362567, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared using General Experimental Procedure A (Suzuki coupling reaction) from 2-bromobenzo[4,5]imidazo[1,2-a]pyrimidine and (1H-indol-5-yl)boronic acid on a 0.12 mmol scale. The crude product was subjected to reversed phase HPLC (TFA buffered water/MeCN) to afford 2-(1H-indol-5-yl)benzo[4,5]imidazo[1,2-a]pyrimidine (T759) as a orange solid (20 mg, 50%). 1H NMR (400 MHz, DMSO-d6): 9.85 (d, J=7.2 Hz, 1H), 8.80 (s, 1H), 8.52 (d, J=8.0 Hz, 1H), 8.46 (d, J=7.2 Hz, 1H), 8.26 (dd, J=8.8, 1.2 Hz, 1H), 7.87 (d, J=7.6 Hz, 1H), 7.77 (t, J=7.2 Hz, 1H), 7.68-7.64 (m, 2H), 7.55 (t, J=2.4 Hz, 1H), 6.70 (m, 1H); MS (ESI) m/z [M+H]+285.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b5462748d73a40be820ef50deee5ed08
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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