Dichloromethane → HCID 67450196, compound

HRID 1853859Notes

Reaction equation

HRID 1853859 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[C:13]4[CH:26]=[CH:25][S:24][C:14]=4[C:15](=[O:23])[NH:16][C:17]=3[CH:18]=[CH:19][C:20]=2[O:21]C)=[CH:7][CH:6]=1)[CH3:4].B(Br)(Br)Br.C(Cl)[Cl:32]>>[ClH:32].[NH2:1][CH2:2][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]3[C:13]4[CH:26]=[CH:25][S:24][C:14]=4[C:15](=[O:23])[NH:16][C:17]=3[CH:18]=[CH:19][C:20]=2[OH:21])=[CH:9][CH:10]=1)[CH3:4]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 67448215HCID 67448215, compound

Product 1

HCID 67450196HCID 67450196, compoundYield 42%

Procedure

Following General Procedure F, 9-(4-(1-aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (120 mg, 0.33 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 5 mL, 5 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 light yellow solid (48 mg, 42%): 1H NMR (500 MHz, CD3OD) δ 7.57 (dd, J=12.7, 6.7 Hz, 2H), 7.47 (d, J=6.9 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.37 (d, J=7.9 Hz, 1H), 7.32 (d, J=7.7 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.15 (d, J=5.4 Hz, 1H), 3.28-3.17 (m, 3H), 1.50 (d, J=6.1 Hz, 3H); ESI MS m/z 351 [C20H18N2O2S+H]+; HPLC >99% (AUC), tR=8.25 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-eb71f7d4ca354691909107dd720c7f9b
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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