Isopropylamine → HCID 21196082, compound

HRID 1066824Notes

Reaction equation

HRID 1066824 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[F:5][C:6]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:7]=1[CH2:8][O:9][CH2:10][C:11]#[C:12][CH2:13]Br>O1CCCC1>[CH:1]([NH:4][CH2:13][C:12]#[C:11][CH2:10][O:9][CH2:8][C:7]1[CH:15]=[C:16]([Br:19])[CH:17]=[CH:18][C:6]=1[F:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 21195964HCID 21195964, compound

Product 1

HCID 21196082HCID 21196082, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of isopropylamine (0.25 ml, 2.9 mmol) was added to a solution of 4-(2-fluoro-5-bromobenzyloxy)but-2-ynyl bromide (97 mg, 0.29 mmol) in tetrahydrofuran (1.4 ml). The cloudy reaction mixture was stirred for about twenty hours, at which time no starting material remained, as determined by thin layer chromatography. The solvents were removed in vacuo. The residue was taken up in methylene chloride and washed with 1 M potassium carbonate. The aqueous phase was back extracted with methylene chloride (2×5 ml). The organic fractions were combined, and dried over sodium sulfate. The solvents were removed in vacuo. The resulting oil was further purified by flash chromatography, affording 78 milligrams (86%) of the title intermediate.

Workup

  1. customThe cloudy reaction mixture
  2. customThe solvents were removed in vacuo
  3. washwashed with 1 M potassium carbonate
  4. extractionThe aqueous phase was back extracted with methylene chloride (2×5 ml)
  5. dry with materialdried over sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customThe resulting oil was further purified by flash chromatography

Sources & evidence

ORD record
ord-0a33d1eb36254d9e87a90648466aa5a6
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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