Triphenylphosphine → HCID 54088438, compound

HRID 2306686Notes

Reaction equation

HRID 2306686 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25](I)[CH:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:29]([O-:31])=[O:30].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>CN(C=O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:29]([OH:31])=[O:30])[CH:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 2723810Sodium FormateHCID 21952131(1-Benzyl-1H-indazol-5-yl)-(6-iodoquinazolin-4-yl)-amine

Product 1

HCID 54088438HCID 54088438, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1-Benzyl-1H-indazol-5-yl)-(6-iodoquinazolin-4-yl)-amine (0.48 g) in DMF under CO was treated with sodium formate (0.1 g) and catalytic quantities of triphenyl phosphine and bistriphenylphosphine palladium (II) chloride at 110° C. The mixture was cooled, added to 5% sodium hydroxide and extracted with ethyl acetate. The aqueous phase was treated with 2N HCl and the precipitated solid filtered and dried to give the title compound (0.07 g); δH [2H6]DMSO 13.35(1H, bs), 10.40(1H, s), 9.30(1H, s), 8.60(1H, s), 8.30(1H, d), 8.17(2H, d), 7.84(1H, d), 7.72(1H, s), 7.30(5H, m), 5.70(2H, s); m/z (M+1)+ 396.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. additionThe aqueous phase was treated with 2N HCl
  4. filtrationthe precipitated solid filtered
  5. customdried

Sources & evidence

ORD record
ord-8acb8f3b24624e919a8c7c664e7e66d7
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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