Dichloromethane → HCID 68516494, compound

HRID 2241321Notes

Reaction equation

HRID 2241321 reaction equation
[CH2:1]([N:8]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:19])[CH:13]=1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:21]1[CH:26]=[CH:25][N:24]=[C:23]2[N:27]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[N:28]=[C:29]([CH3:30])[C:22]=12.ClCCl>BrC1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:1]([N:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:21]2[CH:26]=[CH:25][N:24]=[C:23]3[N:27]([CH2:31][C:32]4[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=4)[N:28]=[C:29]([CH3:30])[C:22]=23)=[C:14]([F:19])[CH:13]=1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 68509730HCID 68509730, compoundHCID 685123991-(4-methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 68516494HCID 68516494, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7961BromobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

To a stirred solution of N-benzyl-N-(3-fluoro-4-hydroxyphenyl)acetamide (34 mg, 0.13 mmol) and 1-(4-methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine (29 mg, 0.1 mmol) (prepared in Example 43, step E) in 400 μL bromobenzene in a capped reaction vial was added DMAP (25 mg, 0.20 mmol). The solution was heated to 150° C. overnight. The reaction was cooled to ambient temperature and loaded onto a Biotage 12S column with dichloromethane and eluted with ethyl acetate to provide the desired product as a tan solid (38 mg, 74% yield).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-6a95f4f3bf7248b5b8100a2172efa68c
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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