Ammonium Chloride → HCID 68599379, compound

HRID 2385098Notes

Reaction equation

HRID 2385098 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:2]1=2.C([Mg]Cl)(C)C.[Br:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:22](=[O:34])[C:21]2=[O:35].[Cl-].[NH4+]>ClCCl>[Br:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:22](=[O:34])[C:21]2([OH:35])[C:9]1[C:8]([OH:11])=[CH:7][C:3]2[O:4][CH2:5][CH2:6][O:1][C:2]=2[CH:10]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 91152732,3-Dihydro-1,4-benzodioxin-6-olHCID 28492568HCID 28492568, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 68599379HCID 68599379, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,3-dihydrobenzo[b][1,4]dioxin-6-ol (2.55 g, 16.8 mmol) in anhydrous dichloromethane (100 mL) at 0° C. added isopropylmagnesium chloride (2 M solution in tetrahydrofuran, 10.0 mL, 19.9 mmol). The solution was stirred at 0° C. for 20 min and 5-bromo-1-(pyridin-2-ylmethyl)-1H-indole-2,3-dione (4.85 g, 15.3 mmol) was added. The reaction mixture was stirred at ambient temperature for 16 h, saturated aqueous ammonium chloride (25 mL) was added and the mixture was concentrated in vacuo. The residue was triturated with ethyl acetate (250 mL) and the solid collected by filtration to afford 5-bromo-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-(pyridin-2-ylmethyl)-1,3-dihydro-2H-indol-2-one (7.26 g, 98%) as a beige solid: 1H NMR (300 MHz, DMSO-d6) δ 9.20 (s, 1H), 8.71 (d, J=4.9 Hz, 1H), 8.06 (dd, J=7.80 Hz, 1H), 7.63-7.55 (m, 2H), 7.52 (d, J=8.0 Hz, 1H), 7.35 (dd, J=8.3, 2.0 Hz, 1H), 7.20 (s, 1H), 6.99 (d, J=2.0 Hz, 1H), 6.82 (d, J=8.3 Hz, 1H), 6.16 (s, 2H), 5.09 (ABq, 2H), 4.20-4.10 (m, 4H).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 16 h
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was triturated with ethyl acetate (250 mL)
  4. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-78d212fcb7684725b5e3ea20eae93b22
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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