Acetone cardice → HCID 59594402, compound

HRID 2263693Notes

Reaction equation

HRID 2263693 reaction equation
C(=O)=O.[CH3:4][C:5](C)=O.Br[C:9]1[CH:10]=[C:11]([CH:35]=[CH:36][CH:37]=1)[CH2:12][CH:13]1[C:19](=[O:20])[N:18]([CH3:21])[C:17]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:16]=2[C:15]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[N:14]1.[Zn](CC)CC>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:26][C:24]1[CH:23]=[CH:22][C:17]2[N:18]([CH3:21])[C:19](=[O:20])[CH:13]([CH2:12][C:11]3[CH:35]=[CH:36][CH:37]=[C:9]([CH2:4][CH3:5])[CH:10]=3)[N:14]=[C:15]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C:16]=2[CH:25]=1

Participants

6

Reactant 3

HCID 18522661Acetone cardiceHCID 59594356HCID 59594356, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 59594402HCID 59594402, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (dry ice-acetone bath) solution of (Z)-3-(3-bromobenzyl)-7-chloro-5-(4-methoxyphenyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one (1.21 g, 2.5 mmol) and PdCl2(dppf) [0.22 g] in dry THF (10 mL) was added 1 M Et2Zn (9.3 mL, 10 mmol, 4 eq). After warming to RT, the reaction mixture was stirred at 50° C. until HPLC indicated reaction to be complete. After aqueous workup, chromatography gave 0.95 g (yield of 88%) of title product. 1H NMR (300 MHz, CDCl3) δ 1.22 (t, 3H), 2.62 (q, 2H), 3.55 (d, 2H), 3.70 (t, 1H), 3.84 (s, 3H), 6.89 (d, 2H), 7.03 (m, 1H), 7.1-7.3 (m, 5H), 7.4-7.55 (m, 3H). The following compound was prepared based on the above procedure: (Z)-7-Chloro-3-(3-ethylbenzyl)-1-(4-methoxybenzyl)-5-(4-methoxyphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one. 1H NMR (300 MHz, CDCl3) δ 1.23 (t, 3H), 2.63 (q, 2H), 3.55-3.65 (m, 2H), 3.68 (s, 3H), 3.80 (dd, 1H), 3.83 (s, 3H), 4.59 (d, 1H), 5.63 (d, 1H), 6.61 (d, 2H), 6.85 (d, 2H), 6.88 (d, 2H), 7.04 (dt, 1H), 7.10 (fine d, 1H), 7.13-7.26 (m, 5H), 7.30 (d, 1H), 7.37 (dd, 1H).

Workup

  1. stirringthe reaction mixture was stirred at 50° C. until HPLC
  2. customreaction

Sources & evidence

ORD record
ord-6ddf0afd69934c27ba9996d0ebefccf7
Source dataset
uspto-grants-2010_12
Patent number
US07851465B2

Reaction notes

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