Allyl bromide → HCID 11384960, compound

HRID 1768020Notes

Reaction equation

HRID 1768020 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][CH2:11][N:12]3[CH2:17][CH:16]=[C:15]([C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[NH:20][CH:19]=4)[CH2:14][CH2:13]3)[C:6]=2[CH:27]=1.[CH3:28][CH2:29][CH2:30]CCC.C(Br)C=C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][CH2:11][N:12]3[CH2:13][CH:14]=[C:15]([C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]([CH2:30][CH:29]=[CH2:28])[CH:19]=4)[CH2:16][CH2:17]3)[C:6]=2[CH:27]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8058HexaneHCID 11440776HCID 11440776, compound

Product 1

HCID 11384960HCID 11384960, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{1-[2-(5-chloro-1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole (392 mg, 1 mmol) (obtained from example 32, step 2) in dry THF (50 ml) was slowly added to a stirred suspension of hexane and was washed with 60% sodium hydride (44 mg) at 0° C. After the addition, the reaction mixture was stirred for 30 min and allyl bromide (183 mg, 1.5 mmol) was added. The reaction mixture was stirred for 4 hrs and quenched carefully with ice cold water. The reaction mixture was extracted with chloroform; washed well with water; dried over anhydrous MgSO4; filtered and concentrated. The residue obtained was purified by silica-gel column chromatography by eluting it with 50% ethyl acetate:hexane. Yellow semi-solid. Yield: 156 mg (36%); 432 (M+H); 1H NMR: δ 7.90(1H, s, NH), 7.78(3H,m), 7.26(6H, m), 6.21(1H, s), 5.99(1H, m), 5.13(2H, m), 4.71(2H, m), 3.40(2H, s), 3.15(2H, m), 2.92(4H, m), 2.68(2H, s).

Workup

  1. washwas washed with 60% sodium hydride (44 mg) at 0° C
  2. additionAfter the addition
  3. stirringThe reaction mixture was stirred for 4 hrs
  4. customquenched carefully with ice cold water
  5. extractionThe reaction mixture was extracted with chloroform
  6. washwashed well with water
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue obtained
  11. customwas purified by silica-gel column chromatography
  12. washby eluting it with 50% ethyl acetate

Sources & evidence

ORD record
ord-dd666428e4ca4e708b1b84e57bcc7f2d
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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