Dichloromethane → HCID 66642781, compound

HRID 2108658Notes

Reaction equation

HRID 2108658 reaction equation
B(Br)(Br)Br.C[C:6]1[C:7]([O:20][C:21]2[CH:26]=[CH:25][C:24]([O:27]C)=[C:23]([CH:29]([CH3:31])[CH3:30])[CH:22]=2)=[C:8]2[C:12](=[CH:13][C:14]=1[CH3:15])[NH:11][C:10]([P:16]([OH:19])(=[O:18])[OH:17])=[CH:9]2.Cl[CH2:33]Cl>>[CH3:33][C:7]1([O:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH:29]([CH3:30])[CH3:31])[CH:22]=2)[CH:6]=[C:14]([CH3:15])[CH:13]=[C:12]2[C:8]1=[CH:9][C:10]([P:16]([OH:19])(=[O:18])[OH:17])=[N:11]2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 66642905HCID 66642905, compound

Product 1

HCID 66642781HCID 66642781, compoundYield 80%

Procedure

A solution of boron tribromide (1 M in dichloromethane, 1.3 mL, 1.3 mmol) was added to a solution of 5,6-dimethyl-4-(4′-methoxy-3′-iso-propylphenoxy)indolephosphonic acid (100 mg, 0.26 mmol) in dichloromethane (10 mL) at −78° C. The ice bath was removed and the reaction mixture was warmed to rt. After stirring at rt overnight, the reaction mixture was quenched with ice, diluted with ethyl acetate and washed with water then brine, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (86.3 mg, 80%): 1H NMR (300 MHz, CD3OD) δ 7.18 (s, 1H), 6.97 (d, J=3.0 Hz, 1H), 6.60 (s, 1H), 6.57 (d, J=9.0 Hz, 1H), 6.26 (dd, J=9.0, 3.0 Hz, 1H), 3.22 (heptuplet, J=6.9 Hz, 1H), 2.28 (s, 3H), 2.18 (s, 3H), 1.12 (d, J=6.9 Hz, 6H); Anal. Calcd for (C19H22NO5P+1.5H2O+0.1 C3H6O): C, 56.79; H, 6.32; N, 3.43. Found: C, 56.61; H, 5.92; N, 3.22.

Workup

  1. customThe ice bath was removed
  2. customthe reaction mixture was quenched with ice
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-499d9d2637ae4d5ca1effd8f2d1843a8
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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