tert-Butanol → Tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate

HRID 1502415Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7](C(O)=O)[N:8]=[CH:9]2)=[CH:4][N:3]=1.[C:15]([OH:19])([CH3:18])([CH3:17])[CH3:16].C([N:23]([CH2:27]C)C(C)C)(C)C.C1C=CC([O:35]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:23][C:27](=[O:35])[O:19][C:15]([CH3:18])([CH3:17])[CH3:16])[N:8]=[CH:9]2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 7-chloro-2,6-naphthyridine-3-carboxylic acid (360 mg, 1.8 mmol), tert-butyl alcohol (3.4 mL), N,N-diisopropylethylamine (1 mL, 5.6 mmol), and diphenylphosphonic azide (1.0 mL, 4.5 mmol) in toluene (6 mL) was heated at 110° C. for 1 hour. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 12 g, ISCO, 0-60% ethyl acetate in heptane) to afford the title compound as a pale yellow solid (410 mg, 83%), which was used in the next step without further purification.

Workup

customThe cooled reaction mixture
washwashed with water (50 mL)
customThe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated in vacuo
customto afford a residue that
customwas purified by flash chromatography (silica, 12 g, ISCO, 0-60% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-2da976eb0a8346779ec7c6a9a0a44cdb
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206175B2

Reaction notes

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