Sodium hydride → HCID 86650546, compound

HRID 2066650Notes

Reaction equation

HRID 2066650 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]([OH:22])[CH2:11][CH2:12][N:13]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[N:15]=[C:14]2Cl)=[CH:4][CH:3]=1.[H-].[Na+]>>[Br:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][CH:10]2[O:22][C:14]3=[N:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][N:13]3[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 86650545HCID 86650545, compound

Product 1

HCID 86650546HCID 86650546, compoundYield 87%

Procedure

Ring closure of alcohol 137 with NaH (1.6 equiv.) as in Example 2AA followed by chromatography of the product on silica gel, eluting with 0-0.5% MeOH/CH2Cl2 (foreruns) and then with 0.5-0.75% MeOH/CH2Cl2, gave additional 138 (87%) as a pale yellow solid (see above).

Workup

  1. washeluting with 0-0.5% MeOH/CH2Cl2 (foreruns)

Sources & evidence

ORD record
ord-035f542e6dbd4f3f8b1d9e2a2cb97453
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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