HCID 9916286, compound → HCID 23296000, compound

HRID 1954302Notes

Reaction equation

HRID 1954302 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:34]=[C:33]([CH2:35][CH3:36])[C:18]([O:19][S:20]([C:23]5[S:27][CH:26]=[C:25]([C:28]([OH:30])=[O:29])[C:24]=5[O:31]C)(=[O:22])=[O:21])=[C:17]([CH2:37][CH3:38])[CH:16]=4)[C:4]=2[C:3]=1[CH3:39])[CH:12]=[CH:11][CH:10]=[CH:9]3.B(Br)(Br)Br.C(Cl)Cl.C(=O)=O.CC(C)=O>C(Cl)Cl>[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:16]=[C:17]([CH2:37][CH3:38])[C:18]([O:19][S:20]([C:23]5[S:27][CH:26]=[C:25]([C:28]([OH:30])=[O:29])[C:24]=5[OH:31])(=[O:21])=[O:22])=[C:33]([CH2:35][CH3:36])[CH:34]=4)[C:4]=2[C:3]=1[CH3:39])[CH:12]=[CH:11][CH:10]=[CH:9]3

Participants

5

Reactant 3

HCID 9916286HCID 9916286, compoundHCID 18522661Acetone cardiceHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 23296000HCID 23296000, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At -78° C., to a stirred solution of 5-[4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-diethyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid (0.374 g, 0.644 mmol) in CH2Cl2 (3.74 mL) was added 1M boron tribromide/CH2Cl2 (2.00 mL). After the addition was complete, the dry ice/acetone bath was replaced with an ice water bath and the reaction was stirred for 1.5 h. The reaction was carefully quenched into crushed ice, diluted with H2O and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with 40% EtOAc/hexane to give 0.300 g (82%) of the title compound as an off white solid. 1H NMR (DMSO-d6) δ 1.09 (t, 6 H), 1.59 (s, 3 H), 2.41 (s, 3 H), 2.62-2.73 (m, 4 H), 7.16 (s, 2 H), 7.38-7.47 (m, 3 H), 7.98 (d, 1 H), 8.49 (s, 1 H), 8.68 (s, 1 H).

Workup

  1. additionAfter the addition
  2. customThe reaction was carefully quenched
  3. custominto crushed ice
  4. additiondiluted with H2O
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified on Biotage
  9. washKP-Sil eluting with 40% EtOAc/hexane

Sources & evidence

ORD record
ord-5aa1648208ef4e5e80f9e7a76dfd60a8
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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