Dichloromethane → HCID 17985036, compound

HRID 2118073Notes

Reaction equation

HRID 2118073 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([CH:18]=[N:19][C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[N:23][C:24]([CH3:30])=[N:25]2)([OH:17])[CH2:4][C:5](C1C=CC(Cl)=CC=1OC)([CH3:7])[CH3:6].B(Br)(Br)Br.[C:37]([O-:40])(O)=O.[Na+].Cl[CH2:43][Cl:44]>>[Cl:44][C:43]1[CH:6]=[CH:5][C:4]([CH:18]([C:3]([OH:17])([CH2:4][C:5]([CH3:6])=[CH2:7])[C:2]([F:32])([F:31])[F:1])[NH:19][C:20]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=2[CH:22]=[N:23][C:24]([CH3:30])=[N:25]3)=[C:3]([O:40][CH3:37])[CH:2]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 17985039HCID 17985039, compound

Product 1

HCID 17985036HCID 17985036, compoundYield 62%

Procedure

130 mg (0.28 mmol) of 1,1,1,-trifluoro-4-(4-chloro-2-methoxyphenyl)-2-[(2-methyl-quinazol-5-yl)iminomethyl]-4-methyl-pentan-2-ol is introduced into 5 ml of dichloromethane, and 5.6 ml of a 1 M solution of boron tribromide in dichloromethane is added in drops at −70° C. It is allowed to reach −10° C. within 1.5 hours, then 5 ml of a saturated NaHCO3 solution is added, the phases are separated, the aqueous phase is extracted with dichloromethane, the combined organic phases are washed with saturated NaHCO3 solution and saturated NaCl solution and dried with sodium sulfate. After the solvent is removed in a rotary evaporator, the crude product is chromatographed on silica gel (eluant: dichloromethane/methanol 98:2). 80 mg (62%) of the desired product is obtained as a yellow solid.

Workup

  1. additionis added in drops at −70° C
  2. customthe phases are separated
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. washthe combined organic phases are washed with saturated NaHCO3 solution and saturated NaCl solution
  5. dry with materialdried with sodium sulfate
  6. customAfter the solvent is removed in a rotary evaporator
  7. customthe crude product is chromatographed on silica gel (eluant: dichloromethane/methanol 98:2)

Sources & evidence

ORD record
ord-8d0729769df5440084aa9f4a030bdf37
Source dataset
uspto-grants-2008_10
Patent number
US07442794B2

Reaction notes

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