Boron tribromide → HCID 67450018, compound

HRID 1853860Notes

Reaction equation

HRID 1853860 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1CCCC#N.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([CH:7]([CH2:6][CH3:5])[C:8]#[N:9])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86689540HCID 86689540, compound

Product 1

HCID 67450018HCID 67450018, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure F, 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl phenyl)butanenitrile (80 mg, 0.21 mmol) in CH2Cl2 at 0° C. was added BBr3 (1.0 M in CH2Cl2, 3 mL, 3 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 (4.3 mg, 6%): 1H NMR (500 MHz, CD3OD) δ 7.56 (dd, J=10.8, 4.6 Hz, 3H), 7.43-7.31 (m, 3H), 7.17 (d, J=8.9 Hz, 1H), 6.00 (d, J=5.4 Hz, 1H), 4.15 (t, J=7.2 Hz, 1H), 2.07 (p, J=7.3 Hz, 2H), 1.16 (t, J=7.4 Hz, 3H): ESI MS m/z 361 [C21H16N2O2S+H]+; HPLC 98.5% (AUC), tR=12.2 min.

Workup

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

Sources & evidence

ORD record
ord-ed94655c6e37423d8dda164e5d6d5f03
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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