Boron tribromide → HCID 136140058, compound

HRID 408887Notes

Reaction equation

HRID 408887 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:22]=[C:21]([NH2:23])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:6]=[C:7]([O:11]C)[C:8]=1[O:9]C.B(Br)(Br)Br>C(Cl)Cl>[C:5]1([CH3:13])[CH:6]=[CH:7][C:8]([NH:23][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([C:5]3[CH:6]=[C:7]([OH:11])[C:8]([OH:9])=[C:3]([OH:2])[CH:4]=3)[N:22]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67327308HCID 67327308, compound

Product 1

HCID 136140058HCID 136140058, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An aryl methoxy derivative p-tolyl-[2-(3,4,5-trimethoxy-phenyl)-quinazolin-4-yl]-amine (2, 30 mg, 7.5e-5 mol) was dissolved in anhydrous DCM (minimal volume, not fully dissolved); the round flask was then sealed. BBr3 (76 μl, 0.111 gr, 205 gr/mol, d=1.45, 2 equiv/per methoxy group, here 6 eq. were used 5.5e-4 mol) was added drop wise (from a syringe) and the reaction mixture was stirred at room temperature for 1 h. The degree of conversion was monitored by HPLC until full conversion was achieved, and the reaction was then quenched with methanol and evaporated to low volume. Another wash was performed using methanol, followed by a wash with acetonitrile and evaporation, to obtain 5-(4-(p-tolylamino)quinazolin-2-yl)benzene-1,2,3-triol, 21 (24 mg, 6.6e-5 mol, 90%). m.p>250° C.; 1H NMR (300 MHz, DMSO-d6) δ 2.35 (s, 3H), 6.75 (s, 2H), 7.22 (d, J=8.0 Hz, 2H), 7.35 (d, J=7.5 Hz, 2H), 7.56 (t, J=8.0 Hz, H), 7.82 (t, J=8.2 Hz, 2H), 8.24 (d, J=7.5 Hz, 1H). Anal. (C21H17N3O3) C, H, N.

Workup

  1. dissolutionnot fully dissolved)
  2. customthe round flask was then sealed
  3. additionwas added drop wise (from a syringe)
  4. customthe reaction was then quenched with methanol
  5. customevaporated to low volume
  6. washa wash with acetonitrile and evaporation

Sources & evidence

ORD record
ord-747f0c68711544b5beb822fe3f77c39f
Source dataset
uspto-grants-2014_06
Patent number
US08759363B2

Reaction notes

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