Dichloromethane → HCID 86689538, compound

HRID 1853857Notes

Reaction equation

HRID 1853857 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([C:19]2[C:20]3[C:21]4[CH:35]=[CH:34][S:33][C:22]=4[C:23](=[O:32])[NH:24][C:25]=3[C:26]([CH3:31])=[CH:27][C:28]=2[O:29]C)[CH:16]=[CH:15][C:3]=1[CH2:4][CH2:5][N:6](C)[C:7](=O)OC(C)(C)C.B(Br)(Br)Br.C(Cl)[Cl:41]>>[ClH:41].[F:1][C:2]1[CH:18]=[C:17]([C:19]2[C:20]3[C:21]4[CH:35]=[CH:34][S:33][C:22]=4[C:23](=[O:32])[NH:24][C:25]=3[C:26]([CH3:31])=[CH:27][C:28]=2[OH:29])[CH:16]=[CH:15][C:3]=1[CH2:4][CH2:5][NH:6][CH3:7]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 67449584HCID 67449584, compound

Product 1

HCID 86689538HCID 86689538, compoundYield 67%

Procedure

Following General Procedure F, tert-butyl 2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenethyl(methyl)carbamate (60 mg, 0.12 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 off-white solid (31 mg, 67%): 1H NMR (500 MHz, (CD3OD) 7.63 (d, J=5.4 Hz, 1H), 7.51 (t, J=7.9 Hz, 1H), 7.15-7.06 (m, 3H), 6.20 (d, J=5.4 Hz, 1H), 3.42-3.35 (m, 2H), 3.30-3.10 (m, 2H), 2.80 (s, 3H), 2.57 (s, 3H); ESI MS m/z 383 [C21H11FN2O2S+H]+, HPLC >99% (AUC), tR=8.65 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-a42c2ce73d82478d9c4085e834eff202
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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