2-(Di-tert-butylphosphino)biphenyl → 5-Fluoro-2-[[5-methyl-7-[(1-oxothietan-1-ylidene)amino]quinazolin-4-yl]amino]phenol

HRID 2281104Notes

Reaction equation

HRID 2281104 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[OH:20])=[N:7][CH:8]=[N:9]2)=[C:4]([CH3:21])[CH:3]=1.[NH:22]=[S:23]1(=[O:27])[CH2:26][CH2:25][CH2:24]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:6]2[C:5]3[C:10](=[CH:11][C:2]([N:22]=[S:23]4(=[O:27])[CH2:26][CH2:25][CH2:24]4)=[CH:3][C:4]=3[CH3:21])[N:9]=[CH:8][N:7]=2)=[C:14]([OH:20])[CH:15]=1

Participants

7

Reactant 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 216845701-Imino-1lambda6-thietan-1-oneHCID 23676156Sodium t-butoxideHCID 901224722-[(7-Bromo-5-methyl-quinazolin-4-yl)amino]-5-fluoro-phenol

Product 1

HCID 1177742805-Fluoro-2-[[5-methyl-7-[(1-oxothietan-1-ylidene)amino]quinazolin-4-yl]amino]phenol

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

1.5 g (4.3 mmol) 2-[(7-bromo-5-methyl-quinazolin-4-yl)amino]-5-fluoro-phenol, 0.45 g (4.3 mmol) 1-iminothietane 1-oxide (IV.6), 0.26 g (0.86 mmol) 2-(di-t-butylphosphino) biphenyl, 0.3 g (0.33 mmol) Pd2dba3 and 0.61 g (6.4 mmol) sodium tert-butoxide in dioxane are heated to 80° C. for 3 h. After cooling to RT the reaction mixture is filtered and evaporated. The residue is purified by FC.

Workup

  1. filtrationis filtered
  2. customevaporated
  3. customThe residue is purified by FC

Sources & evidence

ORD record
ord-1c84f241b3364d3fa67417b099ce8b91
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

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