HCID 21193478, compound → HCID 23445653, compound

HRID 1280915Notes

Reaction equation

HRID 1280915 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[C:17]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:16]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[CH2:1]([C:8]1[O:9][C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:16]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21193478HCID 21193478, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 23445653HCID 23445653, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The tide compound was prepared according to the procedure in Example 5, step 3 using (2-benzyl-4,5-dimethyl-furan-3-yl)-(3-cyclopentyl-4-methoxy-phenyl)-methanone (17.7 g, 45.5 mmol) and 1M boron tribromide/CH2Cl2 (34.8 mL) in CH2Cl2. Purification on Biotage KP-Sil eluting with a 2, 5 & 10% EtOAc/pet. ether step gradient gave 6.15 g (36%) of the title compound. 1H NMR (DMSO-d6) δ 1.40-1.46 (m, 2H), 1.59-1.72 (m, 4H), 1.78 (s, 3H), 1.90-1.94 (m, 2H), 2.16 (s, 3H), 3.18 (quintet, 1H), 3.81 (s, 2H), 6.87 (d, 1H), 7.06 (d, 2H), 7.16-7.25 (m, 3H), 7.46 (dd, 1H), 7.55 (s, 1H), 10.33 (s, 1H).

Workup

  1. customThe tide compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with a 2, 5 & 10% EtOAc/pet. ether step gradient

Sources & evidence

ORD record
ord-1171ff105e844f11a98840af216a55c4
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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