3-(Trifluoromethyl)benzoyl chloride → HCID 59860299, compound

HRID 252199Notes

Reaction equation

HRID 252199 reaction equation
[Cl:1][C:2]1[C:3]2[C:4]3[CH:5]=[C:6]4[CH:19]=[N:18][CH:17]=[CH:16][C:7]4=[N:8][C:9]=3[O:10][C:11]=2[C:12]([NH2:15])=[CH:13][CH:14]=1.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26]>ClCCl.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[C:4]3[CH:5]=[C:6]4[CH:19]=[N:18][CH:17]=[CH:16][C:7]4=[N:8][C:9]=3[O:10][C:11]=2[C:12]([NH:15][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[C:22]([C:21]([F:20])([F:31])[F:32])[CH:23]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 59860296HCID 59860296, compound

Product 1

HCID 59860299HCID 59860299, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-11-oxa-7,10-diaza-benzo[b]fluoren-1-ylamine (35 mg, 0.13 mmol) in the dichloromethane (2.0 mL) is added 3-(trifluoromethyl)benzoyl chloride (54.2 mg, 0.26 mmol). After the mixture is stirred for 24 hours at room temperature, it is diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by flash silica gel column eluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (98/2) to give the product as a solid: 1H NMR 400 MHz (DMSO) δ 10.85 (s, 1H), 9.53 (s, 1H), 9.37 (s, 1H), 8.63 (d, 1H), 8.24 (s, 1H), 8.19 (d, 1H), 7.87 (d, 1H), 7.77 (d, 1H), 7.72 (d, 1H), 7.67 (t, 1H), 7.48 (d, 1H); MS m/z 442.85 (M+1).

Workup

  1. washwashed with saturated K2CO3, brine and water
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customis purified by flash silica gel column
  7. washeluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (98/2)

Sources & evidence

ORD record
ord-0df4a5fc0d924b02b9f2d96a21e71cfc
Source dataset
uspto-grants-2011_01
Patent number
US07868018B2

Reaction notes

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