Diisopropylamine → HCID 19361670, compound

HRID 376261Notes

Reaction equation

HRID 376261 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3[O:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)=[CH:18][CH:19]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(NC(C)C)(C)C.C1C(=O)N([Br:40])C(=O)C1>C(Cl)Cl>[Br:40][C:19]1[CH:18]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[O:16][C:15]=1[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 67184N-bromobutanimideHCID 10065530HCID 10065530, compound

Product 1

HCID 19361670HCID 19361670, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(3-cyclopentyloxy-4-methoxyphenyl)-5-(2-pyridyl)furan, (0.5 g) example 2, in CH2Cl2 (3 ml) and diisopropylamine(21 ul) and NBS (0.320 g) were stirred for 20 mins. at room temperature. The reaction mixture was quenched with Na2CO3, extracted with CH2Cl2 dried with sodium sulfate and evaporated in vacuo to afford the title compound as a beige solid in 63% yield. 1H NMR (300 MHz, CDCl3): δ 1.6 (m, 2H), 2.0-1.8 (m, 6H), 3.90 (s, 3H), 4.95 (m, 1H), 7.05 (dd, 1H), 7.23 (m, 2H), 7.43 (m, 2H), 7.85 (dd, 2H), 8.5 (dd, 1H).

Workup

  1. customat room temperature
  2. customThe reaction mixture was quenched with Na2CO3
  3. extractionextracted with CH2Cl2
  4. dry with materialdried with sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-db832e95191a4b6dbc3bdf89507632c6
Source dataset
uspto-grants-2000_02
Patent number
US06020339

Reaction notes

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