Formic Acid → HCID 136204792, compound

HRID 2361483Notes

Reaction equation

HRID 2361483 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]1[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=1)[CH:13]=[CH:12]2)C1C=CC=CC=1.CO.C(O)=O>C1COCC1.[Pd]>[NH:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17]2

Participants

6

Reactant 3

HCID 284Formic AcidHCID 887MethanolHCID 59489481HCID 59489481, compound

Product 1

HCID 136204792HCID 136204792, compoundYield 109.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

T470 To a solution of 2-(6-(benzyloxy)naphthalen-2-yl)-1H-benzo[d]imidazole (73 mg, 0.21 mmol) in THF (2 mL) was added MeOH (2 mL), Pd—C (10%, 30 mg), and formic acid (0.30 mL). The mixture was flushed with argon and sealed in a microwave vial. The mixture was heated at 100° C. for 5 minutes in a microwave synthesizer. The mixture was filtered off Pd—C and the filtrate was concentrated to give T470 as a white solid (60 mg, 94%). 1H NMR (400 MHz, CD3OD): δ 8.46 (t, J=1.0 Hz, 1H), 8.12 (s, 1H), 8.05 (dd, J=8.8, 2.0 Hz, 1H), 7.85 (d, J=9.6 Hz, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.62 (m, 2H), 7.29 (m, 2H), 7.16 (m, 2H); MS (ESI): 261 (M+H+).

Workup

  1. customThe mixture was flushed with argon
  2. customsealed in a microwave vial
  3. filtrationThe mixture was filtered off Pd—C
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f5590ef4e8324f56925e5db246dde9ae
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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