Diisopropylethylamine → HCID 54579086, compound

HRID 874599Notes

Reaction equation

HRID 874599 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[Br:12][C:13]1[C:14]([C:22]2[CH:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=2)=[CH:15][C:16]2[O:20][CH2:19][O:18][C:17]=2[CH:21]=1.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.ClCCl.O1CCCC1.CO.[OH-].[Li+]>[Br:12][C:13]1[C:14]([C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=3[F:11])=[N:26][CH:27]=2)=[CH:15][C:16]2[O:20][CH2:19][O:18][C:17]=2[CH:21]=1

Participants

9

Reactant 3

HCID 81531DiisopropylethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 58487018HCID 58487018, compound

Product 1

HCID 54579086HCID 54579086, compoundYield 73%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (1.7 g, 9.4 mmol) was added to a stirred solution of 12 (1.5 g, 5.2 mmol), Hünig's base (2.7 mL, 2.0 g, 15.7 mmol), and DMAP (64 mg, 0.5 mmol) in dichloromethane (23 mL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (20 mL), methanol (10 mL) and 1.2 M lithium hydroxide solution (12 mL). The mixture was stirred and heated to 65° C. for 30 min then cooled to room temperature, quenched with brine (50 mL), and extracted with dichloromethane (3×100 mL). The combined extracts were dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-20% ethyl acetate in hexane) provided 13 (1.64 g, 73%) as a solid: LRESIMS m/z 433.0 [M+H]+, calcd. for C19H12Br1F2N2O3 433.0.

Workup

  1. stirringThe mixture was stirred
  2. temperaturethen cooled to room temperature
  3. customquenched with brine (50 mL)
  4. extractionextracted with dichloromethane (3×100 mL)
  5. dry with materialThe combined extracts were dried with sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2913b859e5754996867a411f29564eaa
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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