Water → HCID 86664851, compound

HRID 1952517Notes

Reaction equation

HRID 1952517 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][N:7]1[C:11]([I:12])=[C:10]([CH:13]=[O:14])[CH:9]=[C:8]1[C:15]([O:17][CH3:18])=[O:16].N1C2C(=CC=CC=2)C(CCCC[OH:35])=C1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH:13]([C:10]1[CH:9]=[C:8]([C:15]([O:17][CH3:18])=[O:16])[N:7]([CH2:6][C:5]2[CH:19]=[CH:20][CH:21]=[C:3]([CH2:2][OH:35])[CH:4]=2)[C:11]=1[I:12])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 111714784-(1H-indol-3-yl)butan-1-olHCID 86664852HCID 86664852, compound

Product 1

HCID 86664851HCID 86664851, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 1 (0.20 g, 0.43 mmol) in DMF (2.5 mL) was added 4-(1H-Indol-3-yl)butan-1-ol (82 mg, 0.43 mmol) and K2CO3 (60 mg, 0.43 mmol) at room temperature. The resulting mixture was heated at 65° C. for 18 hours. After cooling to room temperature water (3 mL) was added, extracted with EtOAc, washed with brine, dried over MgSO4, and then purified by MPLC (gradient: Hex to EtOAc) to give 0.16 g of the titled compound as an inseparable mixture with 4-(1H-Indol-3-yl)butan-1-ol. It was intended to obtain an ether, but the reaction converted the Br to OH; 1H NMR (400 MHz, CDCl3) δ 9.70 (s, 1H), 7.54 (s, 1H), 7.27-7.2 (m, 2H), 7.04 (s, 1H), 6.87 (d, J=7.0 Hz, 1H), 5.79 (s, 2H), 4.65 (s, 2H), and 3.77 (s, 2H).

Workup

  1. additionwas added
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. custompurified by MPLC (gradient: Hex to EtOAc)

Sources & evidence

ORD record
ord-7f2e694d867f44de87f0c2c5ee39356b
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

Loading…