Lithium Hexamethyldisilazide → 2-(3,5-Dichloropyridin-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),3'-oxetane]-6-yl}ethanone

HRID 2196106

반응식

HRID 2196106 반응식
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C[O:11][C:12]([C:14]1[C:27]2[O:26][CH2:25][C:21]3([CH2:24][O:23][CH2:22]3)[CH2:20][O:19][C:18]=2[C:17]([O:28][CH3:29])=[CH:16][CH:15]=1)=O.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH2:8][C:12]([C:14]1[C:27]2[O:26][CH2:25][C:21]3([CH2:24][O:23][CH2:22]3)[CH2:20][O:19][C:18]=2[C:17]([O:28][CH3:29])=[CH:16][CH:15]=1)=[O:11]

참가 물질

5

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 109538273,5-Dichloro-4-methylpyridineHCID 592867109-Methoxy-spiro[2H-1,5-benzodioxepin-3(4H),3'-oxetane]-6-carboxylic acid methyl ester

생성물 1

HCID 250051682-(3,5-Dichloropyridin-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),3'-oxetane]-6-yl}ethanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Following the general procedure, condensation of 3,5-dichloro-4-methylpyridine (169 mg, 1.04 mmol) with compound 514 (224 mg, 0.8 mmol) in THF (4 mL) in the presence of LiHMDS (2.4 mL, 2.4 mmol) afforded compound 121 as a white solid material after purification by column chromatography (65-80% EtOAc in light petroleum). LC-MS: RT=3.24 min.; m/z 410.07 (M+H)+, 408.19, 410.22 (M−H)−. 1H NMR (DMSO-d6): δ 8.66 (2H, s), 7.45 (1H, d, J 8.9), 6.91 (1H, d, J 9.0), 4.66 (2H, s), 4.57 (2H, s), 4.50 (2H, d, J 6.5), 4.46 (2H, d, J 6.5), 4.36 (2H, s), 3.85 (3H, s).

출처 및 근거

ORD 기록
ord-5534b4acfe4348178091808df4a1662f
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338431B2

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