Methanol → HCID 86673092, compound

HRID 1853331Notes

Reaction equation

HRID 1853331 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[O:10][C:9]([C:18]2[N:23]=[CH:22][N:21]3[CH:24]=[CH:25][CH:26]=[C:20]3[CH:19]=2)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:34][OH:35].CN(C)[CH:38]=[O:39]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:34][O:35][C:38]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([C:18]1[N:23]=[CH:22][N:21]3[CH:24]=[CH:25][CH:26]=[C:20]3[CH:19]=1)=[CH:8][C:7]2=[N:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:39]

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 86673084HCID 86673084, compound

Product 1

HCID 86673092HCID 86673092, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
100 °C

Procedure

In a 75 ml sealed tube were charged 6-bromo-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl-oxime (tert-butyl protected oxime of example 66) (250 mg, 0.60 mmol), palladium acetate (14 mg, 0.06 mmol), 1,1′-bis(diphenylphosphino)ferrocene (68 mg, 0.12 mmol), triethylamine (170 μl, 1.22 mmol), methanol (125 μl, 3.03 mmol) and dimethylformamide (5 ml). The suspension was degazed with carbone monoxide for 15 minutes. The tube was sealed and heated to 100° C. for 18 hours. The mixture was degazed with argon to remove the excess of carbone monoxide and then diluted with ethyl acetate, washed with a saturated solution of ammonium chloride, water, brine, dried over sodium sulfate and concentrated to dryness. The residue was purified by silica gel flash chromatography (gradient cyclohexane/ethyl acetate 0-80%) to yield the title compound as a yellow solid (172 mg, 72%).

Workup

  1. customIn a 75 ml sealed tube
  2. customThe tube was sealed
  3. customto remove the excess of carbone monoxide
  4. additiondiluted with ethyl acetate
  5. washwashed with a saturated solution of ammonium chloride, water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by silica gel flash chromatography (gradient cyclohexane/ethyl acetate 0-80%)

Sources & evidence

ORD record
ord-62c5eb5533a4413fbd57990c2682e7d1
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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