Boron tribromide → HCID 86689539, compound

HRID 1853858Notes

Reaction equation

HRID 1853858 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[C:10]4[CH:23]=[CH:22][S:21][C:11]=4[C:12](=[O:20])[NH:13][C:14]=3[CH:15]=[CH:16][C:17]=2[O:18]C)[CH:5]=[CH:4][C:3]=1[CH:24]([CH3:34])[CH2:25][NH:26]C(=O)OC(C)(C)C.B(Br)(Br)Br>C(Cl)Cl>[ClH:1].[NH2:26][CH2:25][CH:24]([C:3]1[CH:4]=[CH:5][C:6]([C:8]2[C:9]3[C:10]4[CH:23]=[CH:22][S:21][C:11]=4[C:12](=[O:20])[NH:13][C:14]=3[CH:15]=[CH:16][C:17]=2[OH:18])=[CH:7][C:2]=1[Cl:1])[CH3:34]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67450426HCID 67450426, compound

Product 1

HCID 86689539HCID 86689539, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure F, tert-butyl 2-(2-chloro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (120 mg, 0.24 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 15 mL, 15 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 brown solid (40 mg, 43%): 1H NMR (500 MHz, CD3OD) δ 7.65 (ddd, J=9.9, 9.3, 6.1 Hz, 2H), 7.46-7.36 (m, 2H), 7.33-7.27 (m, 1H), 7.18 (t, J=9.0 Hz, 1H), 6.10 (dd, J=28.8, 5.4 Hz, 1H), 3.86-3.66 (m, 1H), 3.29-3.12 (m, 2H), 1.44-1.28 (m, 3H); ESI MS m/z 385 [C20H17ClN2O2S+H]+; HPLC >99% (AUC), tR=9.07 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-1f7ba51bf8ca4ebfa61be735d90e380a
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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