2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 86692897, compound

HRID 2271677Notes

Reaction equation

HRID 2271677 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:18][CH:17]=1.[Cl:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:31]([Cl:44])[C:30]=1[OH:45]>ClCCl.CO>[BrH:1].[Cl:44][C:31]1[CH:32]=[C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:18][CH:17]=2)[CH:34]=[C:29]([Cl:28])[C:30]=1[OH:45]

Participants

4

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 66716226HCID 66716226, compound

Product 1

HCID 86692897HCID 86692897, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Following general procedure F, 1-(6-bromo-4-(4-(pyrrolidin-1-ylmethyl)phenylamino)quinoline-3-yl)ethanone (4.0 g, 9.42 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (4.0 g, 14.13 mmol) to obtain the free base. The purified product was suspended in dichloromethane/methanol (1:1, 40 mL) and HBr gas was bubbled through the suspension until a solution formed. The solution was concentrated to dryness and the resultant solid was triturated with diethyl ether. The mixture was filtered, washed with diethyl ether, and dried to obtain desired product (3.37 g, 52% over two steps) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 12.03 (br s, 1H), 10.59 (br s, 1H), 10.08 (br s, 1H), 9.27 (s, 1H), 8.43-8.27 (m, 2H), 8.112 (d, J=8.8 Hz, 1H), 7.72 (d, J=8.1 Hz, 2H), 7.59-7.47 (m, 4H), 4.47 (d, J=5.3 Hz, 2H), 3.40-3.24 (m, 2H), 3.19-3.02 (m, 2H), 2.56 (s, 3H), 2.13-1.81 (m, 4H); APCI MS m/z 506 [C28H25Cl2N3O2+H]+; HPLC>99% (AUC), tR=4.97 min.

Workup

  1. customto obtain the free base
  2. customHBr gas was bubbled through the suspension until a solution
  3. customformed
  4. concentrationThe solution was concentrated to dryness
  5. customthe resultant solid was triturated with diethyl ether
  6. filtrationThe mixture was filtered
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-44437ff45c1242fca95dee8a172cf5d7
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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