Dichloromethane → HCID 86689537, compound

HRID 1853856Notes

Reaction equation

HRID 1853856 reaction equation
[Br:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[C:5]([C:16]2[CH:32]=[CH:31][C:19]([CH2:20][CH2:21][N:22](C)[C:23](=O)OC(C)(C)C)=[C:18]([F:33])[CH:17]=2)=[C:4]([O:34]C)[CH:3]=1.B(Br)(Br)Br.C(Cl)[Cl:41]>>[ClH:41].[Br:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8]3[S:13][CH:14]=[CH:15][C:7]=3[C:6]=2[C:5]([C:16]2[CH:32]=[CH:31][C:19]([CH2:20][CH2:21][NH:22][CH3:23])=[C:18]([F:33])[CH:17]=2)=[C:4]([OH:34])[CH:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 67450419HCID 67450419, compound

Product 1

HCID 86689537HCID 86689537, compoundYield 21%

Procedure

Following General Procedure F, tert-butyl 4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenethyl(methyl)carbamate (90 mg, 0.16 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 6 mL, 6 mmol) and the reaction was warmed to room temperature for 4 h. The reaction was quenched by pouring onto water or ice-water and the resulting mixture was concentrated and purified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient). The desired product was dissolved in aqueous HCl, concentrated and dried under high vacuum to afford the desired product as a white solid (15 mg, 21%): ESI MS m/z 447 [C20H16BrFN2O2S+H]+; HPLC >99% (AUC), tR=9.26 min.

Workup

  1. customat 0° C.
  2. customThe reaction was quenched
  3. additionby pouring onto water or ice-water
  4. concentrationthe resulting mixture was concentrated
  5. custompurified by preparatory HPLC (C18 silica, acetonitrile/water (with 0.05% TFA) gradient)
  6. dissolutionThe desired product was dissolved in aqueous HCl
  7. concentrationconcentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-afd70e7463d14953940bf2df68d73669
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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